By Mike Savage, New Canaan collector of sneakers

Forget diamonds, folks. The real treasures these days are nestled between toes and secured with fancy laces. Welcome to the wacky world of rare sneakers, where a single shoe can cost more than your used car and a complete collection might fetch you a small island. 

The niche collector category actually boasts a variety of global collector communities around the world. But every unique collector shoe has a unique value to the collector in all of us.

Buckle up, sneakerheads and curious onlookers alike, as we take a hilarious romp through some of the most valuable kicks ever to grace asphalt (or, more likely, pristine display cases).

Here are some of my favorite sneaker stories.

1. The Moon Shoe: Giant Leap for Sneakerkind (and Your Wallet)

Moon Shoe sneaker 

Imagine a shoe so rare, it predates the internet (gasp!). That’s the moon shoe, a 1972 prototype crafted by Bill Bowerman, the co-founder of Nike, using his wife’s waffle iron. Yes, you read that right. Waffles. Only 12 pairs were ever made, and one recently snagged a cool $437,500 at an auction. Talk about sole-searching!

2. Air Jordan 1 “Chicago”: His Airness, His Kicks, His Millions

Air Jordan 1 Chicago sneaker 

Michael Jordan’s iconic “Chicago” Air Jordan 1s are like the Mona Lisa of sneakers. Released in 1985, they were banned by the NBA for being “too colorful,” which, of course, only boosted their mystique. Today, a pristine pair can set you back a casual $100,000. Just remember, these babies are for admiring, not slam dunking.

3. Kanye West’s Air Yeezy 1 “Prototype”: From Grammy Stage to Auction Block

Kanye West Air Yeezy 1 Prototype sneaker 

Before Kanye became a fashion god (debatable, we know), he was just a rapper with a killer shoe deal. His Air Yeezy 1 prototypes, the ones he wore at the 2008 Grammys, are now sneaker holy grails. One pair fetched a whopping $1.8 million in 2021. So, next time you see Kanye rocking some outrageous kicks, remember, he could be walking on a small fortune.

4. Nike Dunk SB Low Paris Bernard Buffet: When Art Meets Soles

Nike Dunk SB Low Paris Bernard Buffet sneaker 

These Dunks aren’t just sneakers; they’re tiny masterpieces. Created in collaboration with the French artist Bernard Buffet, only 200 pairs exist, each featuring his signature swirling brushstrokes. And the price tag? A cool $90,000. Talk about expensive feet!

5. Solid Gold OVO x Air Jordans: Bling for Your Soles (and Your Bank Account)

Solid Gold OVO x Air Jordan sneaker 

If you’re looking for sneakers that scream “I’m rich and fabulous,” then look no further than the solid gold OVO x Air Jordans. Dripping in 24k gold and diamonds, these beauties were a gift from Drake to his October’s Very Own co-founder Oliver El-Khatib. Price tag? A cool $2 million. But hey, at least they’ll never rust!

So, why are these sneakers so valuable? It’s a cocktail of factors: limited production, cultural significance, historical importance, and a healthy dose of hype. They’re like tiny time capsules, capturing a moment in sneaker (and sometimes pop culture) history. Plus, let’s be honest, there’s a certain thrill in owning something so rare and coveted. It’s like having your own personal mini-museum on your feet.

But before you start raiding your piggy bank for a pair of moon shoes, remember: these sneakers are for the one percent. For the rest of us, there’s a whole world of amazing (and affordable) kicks out there waiting to be discovered. So, lace up your trusty sneaks, hit the pavement, and create your own sneaker adventure. Just don’t step on any million-dollar masterpieces along the way!

And hey, if you ever do find yourself with a spare $2 million lying around, feel free to send a pair of solid gold Jordans my way. I promise to take good care of them. (With kid gloves, of course.)



Mike Savage from New Canaan is the Founder of 1-800 Accountant that helps businesses with their accounting services and needs through cutting-edge technology and customer support. 

In his spare time, Savage enjoys creating unique koi ponds, building vintage Lego sets, and admiring muscle cars and unique pop art. He and his wife also spearhead the Savage-Rivera foundation to help impoverished families in Honduras.